QSAR of benzene derivatives: Comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens

Journal of Computer-Aided Molecular Design

Volumn 16, Issue 8-9, 2002, Pages 611-633

  Clare, Brian W ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

Benzene; FOPA; Hallucinogen; Phenylalkylamine; QSAR; Quantum; Regression; Symmetry

Indexed keywords

COMPUTATIONAL CHEMISTRY; QUANTUM THEORY; REGRESSION ANALYSIS;

BENZENE DERIVATIVES; DESCRIPTORS; FOPA; HALLUCINOGEN; PARAMETER REGRESSIONS; PHENYLALKYLAMINE; QSAR; QUANTUM; REGRESSION; SYMMETRY;

BENZENE;

1,4 DIMETHOXYNAPHTH 2 YLETHYLAMINE; 2,5 DIMETHOXY 3,4 DIMETHYLPHENETHYLAMINE; 2,5 DIMETHOXY 4 (2 FLUOROETHYLTHIO)PHENETHYLAMINE; 2,5 DIMETHOXY 4 (2 METHOXYETHYLTHIO)PHENETHYLAMINE; 2,5 DIMETHOXY 4 BROMOPHENETHYLAMINE; 2,5 DIMETHOXY 4 CHLOROPHENETHYLAMINE; 2,5 DIMETHOXY 4 CYCLOPROPYLMETHYLTHIOPHENETHYLAMINE; 2,5 DIMETHOXY 4 ETHYLPHENETHYLAMINE; 2,5 DIMETHOXY 4 ETHYLTHIOPHENETHYLAMINE; 2,5 DIMETHOXY 4 METHYLPHENETHYLAMINE; 2,5 DIMETHOXY 4 METHYLTHIOPHENETHYLAMINE; 2,5 DIMETHOXYAMPHETAMINE; 3 ETHYTHIO 4 ETHOXY 5 METHOXYPHENETHYLAMINE; 3 METHOXY 4 ETHOXY 5 METHYLTHIOPHENETHYLAMINE; 3,4 DIMETHOXY 5 METHYLTHIOPHENETHYLAMINE; 3,5 DIMETHOXY 4 BROMOAMPHETAMINE; 3,5 DIMETHOXY 4 ETHOXYAMPHETAMINE; 4 METHOXYAMPHETAMINE; 5 (2 AMINOETHYL) 4,7 DIMETHOXYINDANE; 5 METHOXY 4 METHYL 2 METHYLTHIOAMPHETAMINE; AMPHETAMINE DERIVATIVE; BENZENE DERIVATIVE; HOMOVERATRYLAMINE; INDAN DERIVATIVE; MESCALINE; PHENETHYLAMINE DERIVATIVE; PHENYLALKYLAMINE; PSYCHEDELIC AGENT; SEROTONIN 2A RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANALYSIS OF VARIANCE; ARTICLE; ATOM; COMPUTER; COMPUTER PROGRAM; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; ELECTRONICS; HYDROPHOBICITY; MOLECULAR MODEL; PHARMACOLOGICAL PARAMETERS; PHYSICAL MODEL; PRIORITY JOURNAL; PROBABILITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM THEORY; STEREOSPECIFICITY;

EID: 0036706885     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021966231380     Document Type: Article

References (43)

1. Clare, B.W., J. Med. Chem., 33 (1990) 687.
2. Shulgin, A., Shulgin, A., PIHKAL: A Chemical Love Story; Transform Press: Box 13675 Berkeley, California, 1991.
3. Clare, B.W., J. Med. Chem., 41 (1998) 3845.
4. Clare, B.W., THEOCHEM 507 (2000) 157.
5. Clare, BW., THEOCHEM 535 (2001) 301.
6. Pople, J.A., Beveridge, D.L., Approximate Molecular Orbital Theory; McGraw Hill: New York, 1970.
7. Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., Stewart, J.J.P., J. Amer. Chem. Soc. 107 (1985) 3902.
8. Parr, R. G., Yang, W., Density-functional theory of atoms and molecules, Oxford Univ. Press: Oxford, 1989.
9. Parr, R.G., Pearson, R.G., J. Am. Chem. Soc., 105 (1983) 7512.
10. Mracec, M., Muresan, S., Mracec, M., Simon, Z., Naray-Szabo, G., Quant. Struct.-Act. Relat., 16 (1997) 459.
11. Mracec, M., Mracec, M., Kurunczi, L., Nusser, T., Simon, Z., Naray-Szabo, G., THEOCHEM, 367 (1996) 139.
12. Barfknecht, C.F., Nichols, D.E., J. Med. Chem., 18 (1975) 208.
13. Gupta, S.K., Bindal, M.C., Singh, P., Arzneim. Forsch., 32 (1982) 1223.
14. Domelsmith, L.N., Eaton, T.A., Houk, K.N., Anderson, G.M. III., Glennon, R.A., Shulgin, A.T., Castagnoli, N., Kollman, P.A., J. Med. Chem., 24 (1981) 1414.
15. Mracec, M., Mracec, M., Ann. West Univ. Timisoara, ser. chem., 6 (1997) 15.
16. Mracec, M., Mracec, M., Muresan, S., Bologa, C., Kurunczi, L., Simon, Z., Ann. West Univ. Timisoara, set. chem., 5 (1996) 125.
17. PCMODEL V. 5.0, Available from Serena Software, Box 3076 Bloomington IN 47402-3076 U.S.A.
18. Hyperchem v. 6.0, Available from Hypercube, Inc. 1115 NW 4th Street, Gainesville, Florida 32601-4256 U.S.A.
19. Stewart, J.J.P., Q.C.P.E. Bull., 10 (1990) 86.
20. MOLDEN, written by G. Schaftenaar, CAOS/CAMM Center Nijmegen, Toernooiveld, Nijmegen, The Netherlands.
21. Gaussian 98, Revision A.9, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
22. File Gaussang.zip from the site http://www.chem.uwa.edu.au/research/bclare/
23. Becke, A.D., Phys. Rev., A38 (1988) 3098.
24. Lee, C., Yang, W., Parr, R.G., Phys. Rev. B37 (1988) 785.
25. Hehre, W.J., Radom, L., Schleyer, P. v.R., Pople, J.A., Ab Initio Molecular Orbital Theory, John Wiley & Sons: New York, 1986.
26. Klamt, A., Schüürman, G., J. Chem. Soc. Perkin Trans 2, (1993) 799.
27. Besler, B.H., Merz, K.M,, Kollman, P.A., J. Comp. Chem., 11 (1990) 431.
28. ClogP for Windows, ver 1.0.0. Available from BioByte Corp. 201 West 4th St., Suite 204, Claremont CA 91711, U.S.A.
29. file martha.zip from the site http://www.chem.uwa.edu.au/research/bclare/
30. Metropolis, N., Rosenbluth, A.W., Rosenbluth, M.N., Teller, A., Teller, E., J. Chem. Phys., 21 (1953) 1087.
31. Press, W.H., Teukolsky, S.A, Vetterling, W.T., Flannery, B.P., Numerical Recipes in Fortran, Second Edition; Cambridge: 1992, pp. 436-448.
32. Hansch, C., Maloney, P.P., Fujita, T., Muir, R., Nature (London), 194 (1962) 178.
33. Free, S.M., Wilson, J.W., J. Med. Chem., 7 (1964) 395.
34. Furnival, G. M., Wilson R.W., Technometrics, 16 (1974) 499.
35. BMDP Dynamic, Release 7. Available from SPSS Inc., Headquarters, 233 S. Wacker Drive, 11th Floor, Chicago. Illinois 60606.
36. Daniel, C., Wood, F. S., Fitting Equations to Data; Wiley: New York, 1971.
37. Chatterjee, S., Price, B., Regression Analysis by Example; 1st Ed, Wiley: New York, 1977; pp. 199-200.
38. Forsythe, G.E., J. Soc. Indust. Appl. Math., 5 (1957) 74.
39. Johnson, K.J., Numerical Methods in Chemistry. Dekker; New York: 1980, pp. 262-273.
40. Clare, BW., Supuran, C.T., Unpublished observations.
41. Supuran, C.T., Clare, B.W., SAR and QSAR in Environmental Research, 12 (2001) 17.
42. Supuran, C.T., Scozzafava, A., Briganti, F., Clare, BW., J. Med. Chem., 43 (2000) 1793.
43. Karelson, K. Molecular Descriptors in QSAR/QSPR, Wiley-Interscience, New York, 2000.